Acetohydroxamic acid

Acetohydroxamic acid (also known as AHA or by the trade name Lithostat) is a drug that is a potent and irreversible enzyme inhibitor of the urease enzyme in various bacteria and plants; it is usually used for urinary tract infections. The molecule is similar to urea but is not hydrolyzable by urease;[1] it thus disrupts the bacteria's metabolism through competitive inhibition.

Acetohydroxamic acid
Clinical data
Trade namesLithostat
AHFS/Drugs.comConsumer Drug Information
ATC code
Identifiers
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.008.104
Chemical and physical data
FormulaC2H5NO2
Molar mass75.067 g·mol−1
3D model (JSmol)
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Orphan drug

In 1983 the US Food and Drug Administration approved acetohydroxamic acid (AHA) as an orphan drug for "prevention of so-called struvite stones" under the newly enacted Orphan Drug Act of 1983.[2] AHA cannot be patented because it is a standard chemical compound.[2]

See also

References

  1. Fishbein, W; Carbone, P (1965). "Urease catalysis. ii. Inhibition of the enzyme by hydroxyurea, hydroxylamine, and acetohydroxamic acid". J Biol Chem. 240: 2407–2414. PMID 14304845.
  2. Marwick, Charles (1983). "New drugs selectively inhibit kidney stone formation". The Journal of the American Medical Association. 240 (3): 321–322. doi:10.1001/jama.1983.03340030003001.


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